Esters of compounds of the estrone series and process of making same



Patented Jan. 14, 1941 UNITED STATES PATENT OFFICE ESTERS OF COMPOUNDS OF THE ESTRONE SERIES AND PROCESS OF llIAKING SAME New Jersey No Drawing.

\ 3 Claims.

This invention relates tothe manufacture of new esters of compounds of the estrone series by causing such a compound to react with an acylating agent of the fatty acid series, the acid residue in which contains 5-8 carbon atoms.

Suitable acylating agents are, for example, the fatty acids themselves or their anhydrides, halides or esters formed with alcohols of low molecular weight (re-esterification). The fatty acids used may be of straight chain or branched chain, saturated or unsaturated. The acid component may be a valerianic acid or the like.

Among the compounds of the estrone series suitable for the invention may be named estrone,

equiline or equilenine.

A solution of 1 part of estrone in 3 parts of 25 dry pyridine is mixed in the cold with 1 part of n-valerianic acid chloride. The whole is kept for some time at room temperature. The partially solidified mass is now poured into a diluted sulfuric acid solution; the whole is extracted with Application July 26, 1937, Serial In Switzerland July 30, 1936 ether and the ethereal solution is washed with dilute sulfuric acid, sodium carbonate solution and water. The residue left on the evaporation of the ether is recrystallized from hexane and dilute acetone; the estrone-n-valerate thus obtained melts at 103-105 C.

Instead of valerianic acid chloride another halide of the acid, for instance, the bromide, may be used.

As acylating agents there may also be used compounds which contain the radical of angelic acid, iso-valerianic acid, capronic acid, caprylic acid, and the like.

In an analogous manner there may also be obtained the esters of equiline and equilenine.

The reaction may also occur in the presence of another tertiary base, for example, dimethylaniline, quinoline or the like, or even in the absence of a base.

What we claim is:

1. The fatty esters of compounds selected from the group consisting of estrone, equiline and equilenine, the fatty acid residue in which contains 5 to 8 carbon atoms.

2. The estrone-n-capronate.

3. The estrone-n-caprylate.

KARL MIESCHER. CAESAR SCHOLZ. 

